


Thread Gently

by priscilacross



Category: Gotham (TV)
Genre: Angst, Cw: gender dysphoria and misuse of pronouns, Fluff and Angst, Jim is kinda clueless at the beginning, M/M, Past Jim Gordon/Leslie Thompkins, Trans Oswald Cobblepot, don't hate him, ftm Os
Language: English
Status: In-Progress
Published: 2019-04-04
Updated: 2019-04-03
Packaged: 2020-01-04 08:55:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,196
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18340358
Author URL: https://archiveofourown.org/users/priscilacross/pseuds/priscilacross
Summary: Jim becomes fascinated with Oswald from the moment they first met. He finally convinces Oswald to give him a change, but the gangster is a little reluctant to move forward in their relationship. Jim will have to show Os he's in for the long run.





	Thread Gently

**Author's Note:**

> I'm not sure how I feel about the title?? I was listening to Where Angels Fear To Thread- Disclosure while writing this, and thought why not? This is just such a great song, go and listen to it, but beware, it's not FDA approved. 
> 
> Alternative title suggestions are welcome!!
> 
> AU where Jim didn't go to Blackgate and Oswald didn't go to Arkham.
> 
> You guys if there's anything you find offensive/insensitive I apologize in advance and pls let me know, I'll fix it. 
> 
> Hopefully I did trans!Os some justice. 
> 
> As of right now the rating is T, but it'll probably go to an M for the next part, or maybe an E if I'm feeling ambitious lmao
> 
> Also you might get whiplash times jumps are fast

Jim had wondered what it was about Oswald that simply drew him in. On that fated day, in the back of an alley, seeing his smiling face splattered in blood awoke something inside Jim. Then before he even had a chance to process what it meant, everything went to shit. 

He was ordered to kill  the snitch, and he couldn't fathom killing a creature like Oswald Cobblepot. It would be unfair to humanity. Oswald Cobblepot was not only beautifully handsome, but also incredibly intelligent. Perhaps the most intelligent person he knew in Gotham. He couldn't kill him. 

There was no debate in his mind, the decision was made the moment the orders came. Had it been anyone else, would he have killed them? Probably not, but sparing Oswald's life wasn't simply a morality thing. 

He prayed Oswald made it out of Gotham alive after he threw him into the river with a broken leg. When he saw him at his doorstep, relief washed over him, but anger quickly took its place. Why didn't he leave? He could be safe, away from the dangers of Gotham, living a happy life, shining somewhere else. For someone else. Somehow when he thought of Oswald being with someone, anyone, he got even more angry. He pushed him against the wall in the alley and pressed close to him. He unconsciously pressed his thigh against Oswald's crotch and found it… lacking. Oswald of course pushed him away harshly when their wide eyes met under the streetlights. 

“Hey, you… are you...”

“Stop. I don't want to hear it. You will speak nothing of this day. I won't bother you again. You've made your point clear detective.”

“No, Oswald, wait! Is your name really Oswald?” 

Oswald curled on himself, when Jim reached to grab his shoulder. 

“Don't touch me,” he warned and then Jim heard glass shattering and saw Oswald waving a broken bottle at him.

Jim wanted to do as told, but there was also a curiosity that told him to keep pushing. He knew it was wrong, rude even, but he wanted to press. He wanted to find out more about him… her? They? He desperately wanted to know about who Oswald was.

“What do you want?” Oswald’s shaky whisper came, the bottle fell from his weak grasp.

Jim saw an opportunity and he inched closer. Before he knew what he was doing, he pressed his lips to Oswald's. It wasn't much of a stretch, their faces were already inches from each other. Their lips only touched for a second before Oswald was pushing him again. 

“Don’t touch me,” Oswald repeated this time in a stern voice that left no room for questions. Oswald sighed exasperated and ran a hand through his hair. “If you mention this to anyone, Jim, I swear I will-”

“Then you shouldn’t have come back. You should’ve left like I told you to.”

“You don’t understand, Jim. Like I said before, Gotham is my home.”

-

A few days after that, Jim couldn’t get Oswald out of his head. If that was even his/her name. He knew what he had felt and he just didn’t know what to do with himself. Why was she dressed as a man? Well, he very much  _ looked  _ like a man. Jim would've never thought otherwise. Could it be that it was Gotham itself that drove someone like, well, whoever Oswald was before becoming Oswald, to change? Was it because Gotham was unfair to women that he decided to forgo his own gender identity? No, that wasn't it. Oswald wouldn't let something like gender or people's perceptions get in his way. Woman or man, he would still make the world his. And that was just it wasn't it? He felt more comfortable as a man, because he was a man, and he was going to make the world his. No matter what anyone said. Somehow that notion made him admire Oswald even more. 

God, he felt like an inconsiderate  _ asshole _ . ‘ _ Is your name really Oswald? _ ’ What a stupid fucking question. He needed to apologize, but Oswald didn't want to talk about it. He would find a way, when the time was right. When he finally gets his act together.

Things with Barbara were bad, and he knew it was inevitable that things were just going to get worse especially after what happened with Oswald showing at their doorstep. Him and Barbara never lived in even relatively similar worlds. They were just too different from the start, her parents knew it and that’s why they had insisted she shouldn’t accept his proposal. But they’ve been together for so long, it seemed impossible to end things without hurting her. 

He didn’t want to hurt her, he realized that what he had for Oswald was more than just curiosity. He was literally in every single one of his thoughts and maybe he was obsessing over him, and maybe he felt infatuated with the person that Oswald was, but he also didn’t have any unrealistic goals. He was aware things will be difficult and that there’s still a lot he needed to learn about Oswald as a person, but the glimpses that he has seen leave him completely fascinated and wanting more. 

Fortunately for Jim, Barbara was the one to end things. After he found her and Montoya in bed together, there was a wave of relief that overcame him. 

“It’s okay, Barbara, I’m bi too. I, well, there’s actually someone I’m interested in, and I want you to be happy, so, carry on, I’ll stop by and get my stuff tomorrow if that’s okay.” 

Barbara had found someone else, someone who she’d been with in the past, and perhaps someone she never stopped loving in the first place. Not that her love for Jim wasn’t real, he knew Barbara loved him, enough to go against her parents’ wishes and saying yes when he proposed. But in the end, this was for the best. If they had gotten married, he knew that, no matter how much he loved her, things just wouldn’t end up working out because there was just too much separating them. 

With Oswald, he felt a different kind of connection, something he’d never felt with anyone else before. He didn’t know how to describe it, but he felt safe. He felt like him and Oswald were one and the same. Like he could tell Oswald anything, and he would understand. As time passed, he realized how difficult it was to actually approach him with his feeling, mostly because of his own insecurities. 

Then Lee came along, and Oswald met Ed. He felt like Oswald didn’t want his friendship anymore, he was too busy with Ed, and so Jim found refuge in Lee. But then Galavan happened and once again, he was filled with desire and need and longing and worry for the gangster. He longed to have Oswald in his life. He longing to hold his hand and talk about everything and anything at the end of the day. He wanted to fall asleep in each other’s arms, to feel safe in each other's arms. It was just so weird because he’s never felt so strongly for anyone. It was true, him and Oswald were different, but they were also similar. He's never felt so aligned with anyone else. 

Oswald always looked out for him. Always would give up everything for him. Oswald would give even his love for Jim up, if only Jim was happy with that. He could see it when Oswald said goodbye. Sending him and Lee off, wishing him the best even though Jim knew, to this day, Oswald still thought about that kiss in the alley. He wasn't being conceited, he knew because of the way Oswald looked at his lips every time they talked. He knew because of that enticing glance, when he looked into Jim's eyes. It was almost like Oswald was fighting so hard not to look, but in a moment of weakness his gaze drifted downwards. 

Jim knew because his own gaze mimicked Oswald's. He even went as far as to lick his own lips while staring at Oswald's soft looking ones. And soft they were, even though their lips had only been connected for mere seconds, he got a taste of them and he became addicted. Abstaining from those lips all this time was doing him no good. Sadly, he was usually angry whenever he talked to Oswald. Angry because he couldn't have him, because Oswald was smart enough to not let Jim have his way.

Lee's and his departure got interrupted and he saw an opportunity. If he looked into himself he had already made his choice even before anything happened. He couldn't leave Oswald. 

When Galavan told him he would regret this, he could have laughed.

“I have many regrets, this won't be top of my list.” That was the truth, if there's anything he regrets, it's not coming to Oswald's help sooner. 

They killed Galavan. Seeing Oswald's vicious side again, just like the first time he saw him in the alley, stirred that something inside Jim. Seeing how strong and determined Oswald looked, how pleased yet in pain he looked, he wanted to comfort him. Because no matter how hard he hit, he wasn't getting his mother back. 

“Enough.” 

He didn't do it for Galavan. He did it for Oswald. Vengeance is cruel because no matter what you do, you can never get back what you lost. He didn't want Oswald to suffer more than he already had. 

“Oswald, let's go.” 

After everything was done, he drove him and Oswald back to his apartment. The silence was killing him. He didn't want to take advantage of Oswald in this vulnerable time, but he wanted to comfort him. Not like he needed the comfort, he was sure didn’t need nor want his comfort. Not after the way he's treated him all this time. 

Jim parked outside his building and killed the engine. Neither of them moved for several moments. Waiting to see who would make the first move, who would be the first to say what was on their minds. 

It was Oswald who broke the silence, but it wasn’t what Jim wanted to hear.

“I appreciate all your help tonight, Jim. Give my regards to Lee, and tell her I apologize for delaying your leave. Be safe, Jim, you have a family to take care of now.” 

Oswald’s hand was on the door handle and as he was about to exit the car, Jim reached over and wrapped one arm around the gangster's waist. 

“Come inside,” Jim said almost pleading.

“Jim, I… I can’t. You and Lee…” 

Jim could see the pain reflected in Oswald’s face. Oswald had lost too much. 

“Oswald, please. I know I’ve been an asshole and I know that I treated you like shit, but let me make it up to you. Let me show you… just let me show you I can be good to you.”

“No, Jim. This… it’s not, I’m not… I won’t be a replacement for your women. I’m not a woman, no matter how you look at it, I can’t be what you want me to be for you.”

“Oswald, that’s not how I see you. Look, I’m sorry for that time. I was dumb back then, still am. I shouldn’t have asked that. I... I, I can’t get you out of my mind, and that has nothing to do with your gender or or… how far you are in your transi-”

“Stop! Stop, Jim. Please. You have a family to worry about now, you can’t just, just, leave them.”

“And I won’t, I will love that kid and I’ll give anything for that child, but Lee is not who I want to be with. Oswald, I want to be with you.” 

Oswald snatched his arm away and opened the door in a rage. Jim got out immediate after, he ran around to get to Oswald and held his arm. 

“Let go, Jim. Just let me go,” Oswald’s voice was shaking, clearly talking about more than just letting go of his arm. 

“Please,” Jim pleaded, but let go of Oswald’s arm anyway.

“Lee still thinks you’re coming back to her, and you are,” Oswald said with finality, still turned away from Jim.

“I’ll deal with that later.”

Oswald shook his head, “No, Jim. I'm not going to be your side squeeze either.” 

He watched Oswald leave, his determined walk saddened the detective. But Oswald didn't give him a straight up no for an answer. Jim just needed to get everything in order with Lee. 

He did, he told Lee everything. She wasn't surprised. Apparently, his infatuation with Oswald was pretty obvious, especially when he chose him over a peaceful life with her, away from Gotham. 

It wasn't until the Galavan fiasco had died down that he went to meet Oswald. By then Oswald was on his way to becoming Mayor of Gotham. With Ed by his side. Something about that made Jim's stomach churn. What if Oswald already moved on?

Suddenly Oswald was living in a mansion and Jim didn't want to know how that happened he just wanted to see him. So he went to the Van Dahl estate and surprisingly he was let inside without having to fight. He was escorted to Oswald's office where the man was waiting for him, standing by the book shelves, very obviously pretending to be looking for a random book.

“So, you're going to be mayor now, huh?” so much for a proper greeting. 

“Surprised?” Oswald turned around to face him. “People like me can be successful too, you know?”

“Not surprised, no. I always knew you had it in you. And I know now that you truly have Gotham's best interest at heart. In a way, I guess I always knew, it just took me sometime to accept that your methods can be a little unconventional. People like you?”

Oswald scoffed, “Don't make me say it, James. You know what I mean,” he said, sadness dripping from every word, his eyes downcast.

Jim moved closer to Oswald, “You mean determined? Confident? Or should I say,  _ cocky _ ?” He smirked, moving closer still and Oswald kept retroceding until his back was against the bookshelf. “Attractive?”

The dark haired man gave another sarcastic scoff. Jim took Oswald's chin and raised his face so he was looking at him. 

“Oswald, I mean it.”

“You have no idea what I am, or what I'm capable of.”

“Like I said, your methods may be unorthodox, but your cause is the same. I know you'll help clean Gotham, and if I have to turn my head occasionally for you to do it, I will.”

“That's not what I'm talking about,” he said in the quietest whisper. 

Oswald tried to look away, but Jim had a good grasp on his face and there was nowhere he could run as he was pressed against the bookshelf although if he really wanted, Jim was sure he could push him off like he had done in the alley. 

“I know,” Jim said simply. 

Jim closed the space between them almost as if pulled by magnets. His arms wanting to wrap themselves around Oswald and pull him even closer, but Jim settled for resting his hands at the man's hips. He rested his forehead on Oswald's and sighed with relief at the proximity, wanting more still. The gangster's arms still rested by his sides, he made no attempt to move or push him away. They soaked in the silence and the proximity for a few moments until Jim broke the silence.

“Hi,” he whispered.

Oswald smiled, a tiny shy smile, “Hi.” 

“Can we try this again?” 

The dark haired man gave a minute nod against Jim's forehead. 

“Oh thank God,” Jim breathed out and leaned in to kiss Oswald. 

The kiss felt nothing like it did the first time. This time he wasn't stealing it, this time it was welcomed. Jim also felt Oswald's shy arms wrapping around his body, and he mirror the gangster's actions. 

“I'm sorry for forcing myself on you that day in the alley,” Jim breathed out between kisses. “I don't know what came over me.”

“Mm… it's okay, Jim.” 

“No, it's not,” Jim said seriously, putting a pause to the kissing. Pulling away slightly and holding Oswald's arms. “Oswald, if I ever treat you with even the smallest amount of disrespect, I give you permission to, to, I don't know, put a bounty on my head or something. You deserve nothing but the best.” 

“You're bananas.” 

Jim laughed and hugged him close again. 

“Can I stay the night?” 

He saw panic wash over Oswald's features, his eyes going wide and he started to slip to the side away from Jim's hold. 

“I, I don't know if that's a good idea. Ed's going to be back soon and, and, you have work tomorrow, and I have a speech. Today is simply impossible, James,” he said slipping out of his grasp entirely and walking over to his desk. 

“You're right, I haven't even taken you on a proper date yet. Though when I said stay the night, I really just meant sleeping. It's late, and I don't want to drive home,” Jim said with a smile as he scratched the back of his head. 

“Oh. Then I suppose that's possible. The mansion has many rooms.” 

-

 

Now that Oswald was a “reformed criminal” there was no reason  _ not _ make their relationship public, right? It's what he thought, but Oswald felt it would make the elections unfair as the people would see it as an endorsement, or worse. The gangster, for all it's worth, wanted to win fair and square. But Jim suspected there was more to it. 

Making the relationship public would mean having to release public statements, it meant more visibility, it meant more attention, it meant outside expectations. Jim really wished he could just run to an island where there was only Oswald and him. 

Their first date kept being postponed for one thing or another. If it wasn't something with the campaign, it was something with Ed, or something at the GCPD. Sure, he spent more time at Oswald's place and all, but nothing ever happened. A few kisses here and there and Oswald would completely close off. Jim hadn't even started thinking about unbuttoning Oswald's shirt, when the other man was already panicking. Jim wasn't sure if it was because of his lack of sexual experience or if it was because he wasn't comfortable with his body. For all Jim knew, it was a combination of both. He never asked Oswald if he was the first person he'd dated, he knows Oswald will tell him eventually. Probably on that date they've yet to have. 

Jim has had it. Today was the day. They would go on that stupid date and talk about shit they needed to talk about. It wasn't that he was horny, although he was. He just hated the walls Oswald surrounded himself with. He knew it would take time, but it's been at least a month since that first (second?) kiss in his office when Jim sort of poured his heart out. He needed something more than just kisses and vain conversations about the political weather. Every time he thinks he’s coming to a breakthrough with Oswald, he finds only setbacks. And it wasn’t that he was getting tired, he wanted to keep trying to make this work. He knew it could work, but he didn’t see Oswald trying hard enough. He knew he was being selfish, he wanted to have all of Oswald’s attention, and the man was busy. The man was going to be mayor for God’s sake. Things are only going to get busier. 

Jim marched into Oswald’s office, past the mountains of promotional election buttons and banners, and people making calls. He closed the door behind him, found Oswald sitting at his desk, staring down at some papers, not bothering to look up to greet him. Jim cleared his throat. No movement. He cleared his throat again, louder. 

Oswald was either too engrossed in his reading, or he knew what was coming and was trying to avoid it. Jim sighed and walked behind his desk, he kneeled beside Oswald, and slowed turned Oswald’s desk chair so he was facing him. He draped himself over Oswald’s legs and felt the other man shift uncomfortably. He hugged his waist and laid his head on his lap. 

“Jim, I,” Oswald started and cautiously started petting Jim’s hair. “I have work to do.”

Jim moaned at the touch and pressed closer still. “No, you’re coming with me. I got Ed to clear your schedule for the evening. You have no excuses.” 

“You did what? Jim, there’s so much to do. I can’t believe Ed went along with-” Jim started nudging the other man’s waistband, untucking his dress shirt and slipping his hand to touch the soft skin there. “Jim,” he said almost complaining.

“No. Sorry. It’s happening. I’m even going to wear a nice suit.”

Surprisingly, it didn’t take additional begging for Oswald to fold. He could see the reluctance and uneasiness as the man continued to rub his forearm and wrist. Jim slipped his hand in Oswald’s and squeezed. 

“Hey, it’s going to be okay,” Jim tried to reassure him.

The least he wanted to do was make Oswald uncomfortable. He began to think maybe this wasn’t such a great idea. Maybe Oswald still needed more time. He knows how sure of himself he usually is so seeing him like this was almost a little disconcerting. Of course, everyone has their moments of weakness and Oswald was no exception. Perhaps he needed this, a small push. 

They got to the restaurant where Ed had been nice enough to make a reservation for them. It was nice secluded place, it was definitely more expensive than anything Jim was used to, even when he was dating Barbara. Oswald seemed to fit right in, and him, well he probably just looked like a narc based on how many side eyes he was getting from the esteemed guests. They were led to a private table far in the corner of the restaurant with a view to the outside. They sat across from each other. 

“I hope you’re happy,” Oswald said, no undertone of bitterness in his voice.

Jim smiled, and nudged Oswald’s foot with his own under the table. “It’ll be fun, our first date.”

“Or maybe you'll realize I'm poor company and move on,” Oswald said overly dramatic. 

“Not likely, baby, you're stuck with me.” 

“That's probably what you told everyone who came before me though.” 

It hurt a little. Oswald's comment was based on an educated assumption, but hearing it felt like a jab to the gut. Thankfully, he didn't have to answer to said comment as their waiter came to introduce himself and take their drink order. 

“I can't believe you dragged me into this.”

“You say it like we're doing a bad thing, it's just a date,” Jim responded more than a little hurt. “I get that you're stressed about the upcoming elections, but am I not worth one evening?”

“That's not, Jim, that's not what I meant.”

“Well then explain yourself because you make it seem like this relationship isn't worth much to you, like, like, I'm not deserving of your time. If I didn't know better, I'd go as far as to say you don't want to be with me. Oswald, you literally never seek me out, I'm the one that's always coming after you like a lovesick puppy, and I don't know what I'm doing wrong, but I can't seem to break through to you.”

“I don't think this is a conversation we should be having right this moment.”

“Then when Oswald?”

Silence fell over them and Oswald refused to look up as he continued to stare at his intrinsically folded napkin. Then the waiter came back with their drinks and asked if they were ready to order.

Jim sighed at Oswald's direction, and smiled up to the waiter, “Can we just get two ‘chef's choice’ to go, please?”

“Of course, sir.”

The waiter left and they were alone again, the weight of Oswald's silence settling in. 

“I know you care, Oswald, about me, about us, but I want more. I just wish you would show your affections more.”

“I'm not an affectionate person, Jim, I never even dated before you. I spent my whole life running away from bullies and pretending to be stronger than I felt until I became stronger. I had to be independent, I had to have a tough exterior, I never had time for, for, insignificant things like relationships.”

“Is that how you see this relationship? As insignificant?”

“No, Jim. I'm just trying to make you understand and you're not getting it. How can I be vulnerable with you when you don't get it? I need you to be patient, and if you can't do that for me, then it's best you find someone else.”

  
  
  
  
  


**Author's Note:**

> As you can see there isn't a huge emphasis on gender or gender identity, i guess you could say I'm also... threading gently lmao pls don't hate me
> 
> Next chapter could be spicier depend on how this one is received i guess


End file.
